Holiday houses in Calibogue Sound

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Top-rated holiday rentals in Calibogue Sound

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Guest favourite
Home in Daufuskie Island
5.0 out of 5 average rating, 5 reviews

Daufuskie Paradise: Oceanfront/3 Suites/Huge Porch

Daufuskie Paradise cottage blends luxury, wellness, and oceanfront living just steps from the Atlantic. Thoughtfully designed for comfort, it features three spacious suites with firm Purple® mattresses, 100% cotton bedding, feather pillows, down duvets, and Turkish cotton towels. A whole house NUVO H2O filtration system provides cleaner water for drinking, cooking, bathing, and laundry. Enjoy a gourmet kitchen, expansive screened porch with dining and relaxing amenities and stunning ocean views.

Guest favourite
A spacious living area features a bright and airy ambiance with two comfortable sofas and an armchair arranged around a coffee table. A large sliding glass door creates a connection to the outdoors, offering views of the lush surroundings. A dining area with bar stools is visible in the background.
Condo in Sea Pines
4.74 out of 5 average rating, 120 reviews

Lovely Villa in Sea Pines Hilton Head

🌊 🌴 Location, location, vacation! Welcome to your dream getaway in Bluff Villas, where everything you love about Hilton Head is just steps away. This sunny and spacious 2-bedroom, 2-bath condo is perfectly situated just a minutes walk to the beach, South Beach Marina, the iconic Salty Dog Café, and the South Beach Pool (reopening Summer 2025)! Relax on your private patio overlooking Braddock Cove, unwind in the updated living space, or take a quick stroll to grab an ice cream by the harbor.

Top Guest favourite
The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.
Home in Hilton Head Island
5.0 out of 5 average rating, 123 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Top Guest favourite
A spacious living area is furnished with a blue sectional sofa and a coffee table. Soft lighting is provided by two lamps on either side of the sofa. A large patio door opens to an outdoor seating area, allowing natural light to fill the room.
Apartment in Sea Pines
5.0 out of 5 average rating, 22 reviews

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

Welcome to your home away from home on Hilton Head Island! Stay steps from the beach in this newly renovated 1-bedroom villa with all new furnishings. It is the perfect blend of comfort, convenience, and coastal charm. Nestled just a short walk from the beach and the famous Salty Dog Café, you're in the heart of Sea Pines fun with dining, shopping, biking, pickleball and sun-soaked relaxation right at your doorstep, not to mention nearby access to some of the state’s most iconic golf courses.

Guest favourite
Apartment in Sea Pines
4.86 out of 5 average rating, 14 reviews

Waterfront Sea Pines Studio | Beach & Salty Dog

"Island Therapy!" Waterfront Sea Pines Studio - Steps to Beach & Salty Dog - Sunrise & Marina Views. This serene Hilton Head retreat perfectly located in the Bluff Villas of Sea Pines Resort. At this remodeled waterfront studio you will wake up to stunning sunrise views over the water. You’re literally next door to the famous Salty Dog Café and the South Beach Marina. You’re only a 2-minute walk to the private beach, bike paths, viewing resident dolphins and catching a picture-perfect sunset.

Superhost
Home in Sea Pines
4.92 out of 5 average rating, 13 reviews

Wren's Nest - 4BR SeaPines Retreat+Backyard Oasis

Welcome to Wren's Nest, a luxurious Sea Pines retreat. Just steps to private beach access, this stylish 4BR home blends coastal elegance with family-friendly comfort. Enjoy a secluded backyard oasis with a waterfall pool, large screened-in porch, and space to unwind. Walk or bike to South Beach, shops, restaurants, and miles of scenic Hilton Head trails. Bring the entire family, leave with memories of a lifetime. Beach chairs, wagon, and umbrellas included. Pets welcome.

Superhost
A spacious outdoor deck is seen overlooking a tranquil lagoon, surrounded by tall pine trees. A glass-top table and seating are positioned for enjoying meals outdoors while taking in the serene natural views.
Condo in Sea Pines
4.5 out of 5 average rating, 6 reviews

Lovely Lagoon View Villa Near Beach on Hilton Head

1591 Lagoon Villa — You'll find two cozy bedrooms, two sparkling bathrooms, a fully equipped kitchen, a comfy living and dining area, a handy washer and dryer, and even an outdoor shower. This charming space can easily host up to four guests, which makes it perfect for a small group or family. You'll have everything you need for a comfortable and convenient stay. Enjoy a vacation reimagined with host2coast, your trusted partner in Hilton Head Island Property Management.

Top Guest favourite
A screened-in porch is furnished with a wooden table and four high-backed chairs, offering views of the surrounding greenery. Natural light fills the space through the screens, highlighting a large potted plant and a smaller table. The floor is adorned with a textured blue rug.
Condo in Daufuskie Island
5.0 out of 5 average rating, 89 reviews

Daufuskie Island Beachside Escape • Birdsong Oasis

Accessible only by boat or ferry, Birdsong Oasis is a serene studio retreat with two queen beds featuring luxury Saatva mattresses, a kitchenette, spacious bath, and screened-in porch. Set between the salt marsh and beach in Daufuskie Island’s historic Melrose community, it overlooks the peaceful marsh beneath moss-draped oaks and is just steps from uncrowded white-sand beaches—perfect for swimming, beachcombing, birdwatching, or simply slowing down to island time.

Top Guest favourite
A sunlit exterior area is showcased, featuring a wooden walkway that leads to The Houseboat. Planters with vibrant green plants and flowers are positioned alongside the entrance, contrasting with the clear blue sky and water view in the background.
Houseboat in Tybee Island
4.94 out of 5 average rating, 159 reviews

The Houseboat on Tybee Island

Located at the Tybee Island Marina on Lazaretto Creek, along the western boundary of Tybee Island, The Houseboat offers spectacular sunrise and sunset views nestled in a serene spot between the beach on Tybee or a day exploring Savannah. Due to its location on a floating dock in a tidal creek, with low tides making for a difficult/steep transition between the floating and stationary docks, The Houseboat is not ideal for guests with mobility issues.

Guest favourite
A private deck is shown with comfortable seating overlooking a serene landscape. Lush trees frame the view, which includes sunset skies and ocean waters in the distance. Natural light enhances the tranquil setting, inviting relaxation and outdoor enjoyment.
Condo in Sea Pines
5.0 out of 5 average rating, 6 reviews

Oceanfront Villa @ Sea Pines | Steps to Beach

Set off on your perfect island escape in this serene oceanfront villa tucked within Sea Pines’ South Beach Marina. Wake up to coastal breezes, unwind on your private deck at sunset, and enjoy direct beach access just steps away. Designed for easy, relaxed living, this spacious two-story retreat is ideal for families or groups. Walk to the iconic Salty Dog Café, enjoy the pool, and explore nearby tennis, pickleball, and scenic bike paths.

Guest favourite
A spacious kitchen features rich wooden cabinetry and a large granite countertop with an undermount sink. Pendant lights illuminate the area, which opens to a well-lit dining and living area through large windows. White pillars add elegance to the open design.
Townhouse in Sea Pines
4.91 out of 5 average rating, 153 reviews

HHI South Beach at it's Best! Sea Pines

The two story floor plan has 4 bedrooms, 4.5 baths. The lower level has a garage, three bedrooms, three bathrooms and a covered porch. Upstairs you will find the main living area, gourmet kitchen, dining area, 2 decks, the master bedroom/bathroom, laundry room and half bath. There’s an open floor plan that flows from the kitchen to the dining room right out to the balcony overlooking Braddock Cove and the South Beach Marina.

Top Guest favourite
A charming circular home is nestled among tall trees, featuring a spacious deck with white lounge chairs. The wooden steps lead up to the entrance, showcasing large windows that allow ample natural light. The surrounding greenery enhances the sense of privacy and seclusion.
Treehouse in Sea Pines
4.98 out of 5 average rating, 103 reviews

Harbour Town Tree House | Private Office | HT Pool

Please see our almost 1000 5-star reviews at our other properties. Enjoy unbelievable tranquility high in the Sea Pines tucked away on Deer Island next to Harbour Town. Walk to the shops, restaurants, entertainment, and the Yacht Basin in just minutes. Feed the deer from your hand while you connect with nature. The Sea Loft is just one house away from the Turtle Trail that winds along the marshlands.

Popular amenities for Calibogue Sound holiday rentals